Editor’s Question: What has been your biggest failure during your career and how has it helped you succeed?

Editor’s Question: What has been your biggest failure during your career and how has it helped you succeed?

Believe it or not, this Editor’s Question was a difficult question to get responses to. During my time as editor, and especially when reading the Get to Know answers, I often hear how very successful people emphasise the importance of making mistakes and learning from them. Which is where the idea for this question came from – it wasn’t to get leaders to dwell on their mistakes but to hopefully get an insight into how these failures have made them the successful leaders they are today.

And thankfully, four leaders answered my call and have spoken openly about their failures and what they have learnt from them. Dean Sadler, CEO of Tribepad, begins with his answer below:

It was 9:15am on June 16, 2000, and I was working at Plusnet, where I began my career. Someone in customer support asked me to do something quickly as I was dropping into the office for 15 minutes. It was my 30th birthday and had plans to go out for the day with my future wife.

Best laid plans, but eight hours later I’m still in the office fixing the problems I caused with a missing where clause in an SQL statement. I had managed to change the password for over 450,000 customers in less than two seconds. And of course, within a minute the phone system went nuts as people couldn’t connect to the Internet until I restored a previous backup of that table. It caused huge problems for customers who couldn’t work or play at home, for businesses who used Plusnet to operate effectively and for Plusnet who prided themselves on great customer service – and were failing to deliver. All because of me.

The following day I started to automate the entire backend platform so that I would never have to write an SQL statement again and that’s how Plusnet became one of the most automated ISPs in the UK at the time. It’s something that I insisted on at Tribepad, and we pride ourselves on having efficient and effective technology that delivers against business objectives.

So, what did I learn? Firstly, to check and check again when creating code or systems that impact other people. Diligence is key in all industries, and especially in any sector that is customer facing and affects real people with real issues. Secondly, to document the process so it’s easy to go back and find out where there have been issues. As well as this, it was clear to me the value that comes from automation and writing programmes that reduce friction, leave minimal room for error and how this can be so powerful for businesses and the people they serve. Which is what we do at Tribepad and have seen its benefits for staff, customers and their clients. 

It might have been my worst birthday ever, but she still married me, and it set me and the business up for success, so there are silver linings all round. I now try not to work on my birthday. It’s better for the soul.

Mena Migally, Regional Vice President – Emerging EMEA, Riverbed:

While I have been very fortunate in my career, there was a clear low point which fundamentally shaped both its trajectory, as well as my personal growth and self-confidence. As is most often the case, this was the result of significant change, which while I had proactively pursued, I had most certainly underestimated.

After finding success over nearly a decade at a large, multi-national, multi-faceted IT corporation, I decided to take the ‘plunge’ into an exciting venture. Though this was of a smaller scale, it offered great promise. The decision to willingly leave my comfort zone was difficult, especially as I had been advised against it by many. But I felt convinced it was the right move at the right time – I had extensive experience in the technology I was selling, deep knowledge and experience in operational excellence and had built strong personal and professional values.

Filled with naïve enthusiasm, I decided to trust my instincts. My excitement was soon tempered by a harsh reality check, as I quickly realised I needed to adapt not only to a new company with a different product set, but a fundamentally different scale of operations. This meant a higher degree of uncertainty in every avenue – be it dealing with customers, partners or even colleagues. The realisation that the ‘sale’ was not going to come easily and required infinitely more ‘smart effort’ quickly dawned on me and made me question my decision to leave my comfort zone. Falling back on past expertise, I tried everything I learned from my previous company. And while the effort was there, the results were slow and not up to my expectations. Thoroughly demotivated – and based on advice to ‘jump ship’ back to familiar territory – I contemplated making a move.

While the easy path out was certainly alluring, I woke up one day deciding not to give up. I had to prove to myself that I could in fact succeed before I closed that chapter. This ultimatum challenged me to think differently, and I subsequently pursued closure on a large and complex deal that I made known to a colleague. Having him in my corner meant he soon became my champion inside the company. This deal opened the eyes of everyone to the potential at hand – but more importantly to me personally, when I closed it, I proved my abilities and resilience, which gave me the confidence to move on in my career with a greater sense of self-worth.

Perhaps the most defining moment in all this was my decision to make myself vulnerable in transparently discussing my plans with my champion (who now, even nine years on, remains my mentor, manager and friend). He quickly moved in the background to finally offer me a job reporting to him, which I gladly accepted. This changed the trajectory of my career, allowing me to thrive and grow.

Henry Ford famously said: “The only real mistake is the one from which we learn nothing,” and in that respect, I don’t look back at this experience as a mistake. I learned valuable lessons which have served me well ever since. Never give up on your values if they are strong. Know your strengths and build on them, rather than only working on improving your weaknesses. Be adaptable to change, while being full of intent in finding out how to make the change easier with proper research. Find a champion and mentor who understands and embodies the values that you hold dear. And most importantly, through it all, never give up!

Fred Crehan, Area Vice President Growth Markets, Confluent:

As a leader in the tech industry, I have experienced many ups and downs throughout my career. While success brings its own rewards, it is often the failures that teach us the most valuable lessons. I would like to share some of the lessons learned and how they have helped shape my career.

Early in my career, as an individual contributor in sales, unsurprisingly, I was solely focused on driving sales results. The ‘what’ and the ‘when’ of the deal was all that mattered and I paid very little attention to ‘how’. I would put in a lot of effort and long hours into every deal, and would set myself high standards for success. However, this approach did not systematically bring success – one very large deal in particular did not go according to plan and I lost it. After claiming everything was under control, the loss was quite a burden to my confidence. I felt I had let down my manager and my team, as well as myself.

Looking back, my biggest mistake was not involving the right people at the right time. I was so focused on closing the opportunity myself to the forecasted time and budget, that I failed to seek input and feedback from the people who could have helped me see the challenges. I also failed to communicate effectively with my team, which led to misunderstandings and mistakes.

Looking back at that time in my career, I have to say, the failure was a turning point for my own development. It forced me to reflect on my leadership style and to recognise the importance of collaboration and communication in solving complex problems. It was also a valuable lesson to reflect and learn how important it is to focus on the ‘how’ instead of just the ‘what’ and the ‘when’. 

Furthermore, for my own growth, it was important to admit my own failure which helped me to develop resilience and a growth mindset. If you look at it from a higher perspective and treat every failure or mistake as a learning opportunity, you can’t lose. You will never lose. You either win or you learn. 

Today, as Area Vice President Growth Markets at Confluent, I am grateful for the lessons I learned. Since the experience many years ago, I have gone on to value coachability and collaboration as the most important attitude traits for winning teams. I believe that it has really helped me to become a better leader. I encourage all leaders to embrace and encourage failure as it is merely another step towards success and to build winning teams full of highly coachable and collaborative superstars.

Griff Parry, CEO, m3ter:

I’m lucky in that I’ve avoided any ‘showy’ failures, but I’ve failed an awful lot, and continue to do so. 

I’ve learned to think about failure as a constant and as a positive, because if you’re going about things the right way and pushing the boundaries, failure’s what happens. It creates an opportunity to learn, adapt and improve.

I wish I’d learned to embrace failure a little earlier, because I spent too long at the start of my career playing safe and avoiding putting myself in situations where things might go wrong.  That meant I didn’t conspicuously fail, but also meant I didn’t learn and progress as fast as I could have done. 

There’s another angle though. Being prepared to fail is one thing, but you need to be resilient to it too. If failure’s part of the process, you have to commit to it – you can’t be embarrassed about it, or deny it, or let it get you down. You need to absorb the learning, pick yourself up and keep going. I like the Beckett quote which captures this nicely, which I find motivating: “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”  

For me, failure is an integral part of my journey as an entrepreneur, and I’ve come to view each mistake as a stepping stone rather than a stumbling block.

When starting and running a business, failure is not only inevitable but necessary. If you’re doing it right, failure should be constant because you’re pushing the boundaries and testing processes you’ve not tried before. The key is to learn from it quickly, without recrimination or blame, and avoid repeating the same mistakes again. Grit counts for a lot, especially for start-ups where it’s all about learning and iteration. You have an idea, you test it, you learn and you adapt. It’s a constant process. Having the resilience to keep going and maintain energy levels really matters. 

People are also drawn to start-ups because of the adventure and the excitement of building things, which is why they are often highly invested. That’s founder-type behaviour, so treat them as someone cut from the same cloth. 

To succeed in the start-up landscape which is unpredictable, and often turbulent, you need to be adaptable and resilient. Failure pushes you to overcome it in innovative ways. Ultimately, it’s just another stepping stone towards success.

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